EPISODE 251

Why small upgrades beat big goals every time

 

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This month we’re talking about upgrades and goal setting and I know this makes some people freeze, procrastinate, or secretly worry you’ll disappoint yourself.

So, in this week’s episode of Chill & Prosper, I’m talking about incremental upgrades - small, symbolic changes that help you grow without burning out or psyching yourself out.

We cover:
✨ Why perfectionism often disguises itself as “doing it the right way”
✨ How tiny upgrades help your nervous system feel safe with more money
✨ Why big, unrealistic goals can backfire (and what to do instead)
✨ How to acclimatise yourself to success instead of sabotaging it
✨ Simple, practical upgrades that create momentum fast

You don’t need to overhaul your entire life this year.
You just need to choose the next upgrade.

xx Denise

P.S. Haven’t grabbed your free New Year Upgrades & Money Goals Workbook yet?

Get it now at denisedt.com/jan and get clear on where you want to upgrade and grow this year. 

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Transcript

Prefer to read?  Here's the transcript for this episode:

Hey, hey, it's Denise here. Welcome to this episode of Chill and Prosper. And we're still in that new year and new you, January energy. So I just want to remind you of our free gift for this month. It is our money, goals and upgrades workbook. You can get that at DeniseDT.com/jan as in January. And that will help you kind of set the tone for the year. You know, and don't worry if you're listening to this and it's not January, you can still grab that at DeniseDT.com/jan.

On today's episode we're talking about the power of incremental upgrades, especially if you're someone who resists setting goals for fear of not achieving them. Right. And that's one of the questions I get asked actually a lot: should I set really, really big goals that are big stretch goals or should I set more realistic goals?

And to be honest, there's no right or wrong way to set goals. And sometimes we get really caught up in that. And I'll get people who ask me, should I write my goals in present tense or past tense? Should I write them as if they've already happened? Or should I do SMART goals? Or what is the perfect way?

And often that becomes a bit of procrastination. And I say this a lot, right? It's this perfectionism that leads to analysis paralysis and you just end up doing nothing. We're so worried about getting it wrong all the time. And you really can't.

The intention behind goals is literally intention and focus. If you know what you're playing for, then you focus your energy on it, right? You set your brain in motion—your reticular activating system—to look for opportunities and to seek out answers. And that's just how our brains work.

So let's talk about a little bit more of a sustainable, maybe gentler way to set goals this year and to have a path to progress. Because I really don't want you to psych yourself out, get stuck in analysis paralysis. And also, I don't want you to get stuck in having very vague, wishy-washy goals this year either.

Because when we send out vague, wishy-washy intentions, then no surprise—we get vague, wishy-washy things back to us, right?

And if you did my 5x5 Manifesting Challenge last year—which don’t worry, we’re going to do again this year, probably in November again, October/November—we use this analogy of calling up a pizza restaurant and saying, “Hey, send me a pizza.” And they’re like, “What kind of pizza do you want?” You go, “Whatever, just send me pizza. Surprise me. A big one.” And they’re like, “But what do you want?”

So they might just go, “Okay, we’ll just send her a margherita pizza.” And you open the door and go, “But I didn’t want a margherita pizza!” And they’re like, “Well, you should have been more specific.” And this is what we do when we set goals often. We go, “Hey, universe, send me more money. I just want more money, more clients.”

And the problem is we find a coin in the street, we get a $5 scratchie lottery win, or we get clients that we don’t want anymore, and we’re like, “I didn’t mean that!” And the universe is like, “Well, you should have been more specific.”

That’s why I advocate getting specific. But you can still leave room for surprise sometimes. The more you can set your intentions and be clear about what you’re playing for, the better.

Let’s talk about setting really big stretch goals. I remember someone saying to me one year, “I want to make $1 million this year,” and I’m like, “That’s cool!” I love that we can just normalize talking about that. So I asked, “Okay, awesome—where are we starting from?”

She had no products and services, had never made more than a couple of thousand dollars. I’m not saying that’s impossible—but there is some realism to consider. I asked: “How many people are on your list? What avenues have you got for people to send you money? What passive income do you have? What services are you going to do this year? How many clients do you want? How big is your list size?”

It’s not being a Debbie Downer—it’s just saying, “Let’s get real about what’s possible in a year.” If you want to make $1 million, we need a plan: how many units, what kind of marketing, building your list... big effort. Otherwise, those huge goals can set you up for failure.

But the flip side I see sometimes—especially with Accumulator personalities or Nurturers—is a little bit of scarcity thinking and confidence issues. People say, “But what if I don’t hit it? I’ll be disappointed.” And I always say, “The Goal Police aren’t going to come knocking on your door and say, ‘Oh my god, you didn’t hit your goals—off to jail!’”

That doesn’t happen, right? And most of the time, nothing really bad happens. You just go, “Okay, cool—I can recalibrate.” But sometimes in striving for something big, you make momentum that might pay off next year, or the year after.

So we’re trying to find that middle point—that sweet spot—between being excited about a big goal and motivated to take action you wouldn’t normally take, while still giving yourself small wins to keep your confidence high.

That’s where incremental upgrades come in.

In Money Bootcamp, if you haven’t heard me talk about that term before, incremental upgrades are a way of:

• Feeling good
• Taking action (even when stuck in analysis paralysis)
• Acclimatizing to more good feelings, wealth, and joy

Because often the problem isn’t strategy—it’s that feeling of “too much.” When people start to earn more than their family ever has, or reach a new level, their nervous system doesn’t know how to handle it.

It can feel alien. Like moving into a new social class. And your system might say: “Abort! This feels unsafe.”

That’s why I use the Olympic athlete analogy. If the Olympics are in a high-altitude city, you train at altitude. You acclimatize. Otherwise, you’ll feel sick. And that’s what happens when someone wins the lottery or makes a huge leap—they haven’t adjusted.

So incremental upgrades help you feel good while gradually stretching your comfort zone. They also trick your brain—it doesn’t feel like a big, dramatic leap. And that helps during the lag period between where you are and where you want to be.

Just a reminder—go download the workbook because it will help you go through this process and decide what to upgrade next. That’s at denisedt.com/jan. Do it today so you don’t forget!

You might have had experiences in the past where you set goals and didn’t achieve them—and felt disappointed. But you also might remind yourself of times when you strived for something big and it paid off later.

So this doesn’t have to be an all-or-nothing approach. It’s not binary. And I don’t want you to burn out in the first quarter. I want you to feel like, “I’ve got a whole year to achieve my goals. I can pace myself. I can set myself up for success.”

Also—I can give myself the tools I need to thrive this year. I don’t have to suffer for it. I don’t have to work really hard. I don’t have to put myself in a sink-or-swim situation.

Let’s talk a bit more about that “sink or swim” energy. Some money archetypes—like Alchemists, Mavericks, sometimes even Rulers—have this internal programming that says, “I’ll only work hard if I deny myself” or “the creative muse only visits me when I’m suffering.”

It’s that belief: “It can’t be easy.”

If you’re not sure what I’m talking about, I’ll be referencing money archetypes a lot on the podcast this year. If you haven’t done it yet, go take the free quiz at denisedt.com/quiz so you know what your money personality is.

That way, when I reference the archetypes, you’ll understand how this stuff shows up for you.

So some of those archetypes really operate in extremes—0 or 1000, nothing in between. Or they think, “If it’s not dramatic or urgent, it doesn’t count.”

But it’s totally okay for you to set sustainable goals. Ones that feel like you. It’s okay to find the middle ground.

The other thing to think about is: what goals this year are truly yours—versus goals from an old version of you, or someone else’s expectations?

This could be a money goal, a business goal, a life goal—or just the way you run your business. A lot of us click over into the new year without questioning anything. We assume, “This is just how I do things,” or “This is what people expect of me.” But everything is up for negotiation.

I’ve got a podcast episode (either already released or coming up) about New Year, New Prices. This is a great time to rethink your pricing. Are your prices truly yours—or are they based on your industry? Your competitors? Your mentors?

It’s okay to go, “I’m letting that influence go this year.” That can feel amazing.

Here’s the thing: incremental upgrades—upgrading symbolic parts of your life—often beat big overhauls or lottery-winner fantasies.

So many of us think: “One day a big windfall will come and everything will be perfect.” Or: “When I hit my million-dollar year, everything will magically align.” But it doesn’t work like that. You’re still you.

Whether you’re making $10K or $10 million, you’re still going to be yourself. So what we want is confidence, consistency, and sustainable success—the kind that feels solid and grounded.

That’s why I help people shift their energy in subtle, but powerful ways.

In Money Bootcamp, one of the first things we do is an inventory of your life. We ask: Is this economy class? Premium economy? Business class? First class?

It’s arbitrary, sure—but you know how those categories feel.

There might be things in your life that feel economy class—not your choice, but they make you feel poor or inconvenienced.

There might be some things that feel like a small step up—premium economy.

Some things might feel like business class—flowy, easy.

And maybe a few things feel first class—high vibe, luxurious, fully aligned.

Sometimes people say, “I can’t think of anything that feels first class.” But often they’ll realise something does—maybe their friendships, or their mindset support.

When you take stock of this, you’ll see areas where you’re being held back, inconvenienced, or drained. Some of those things you can’t upgrade yet, and that’s okay. But there are always upgrades you can make.

Sometimes those upgrades will cost money—like if you want to hit six figures but you’re working on a super slow laptop in a shared noisy space. Maybe you can’t afford a $3,000 MacBook today, but maybe you can upgrade something. It could be symbolic: a better chair, a mouse that doesn’t hurt your wrist, a lap desk.

These small upgrades show the universe—and yourself—that you’re serious.

And if you’re not sure what you want to earn this year, or what your big goals are, that’s totally okay. That’s exactly where incremental upgrades are most useful. They snowball. You do one, it feels good, and then you do another. You don’t have to overhaul your whole life all at once.

You can start with:

• The things that inconvenience you most
• The areas that are most symbolic of where you want to go
• The lowest hanging fruit

This approach works for all personality types—whether you’re super strategic or just intuitive.

Okay, now let me give you some examples of symbolic upgrades.

You might suddenly realize there’s something in your environment you’ve been putting up with forever. Maybe your chair gives you back pain. Maybe your workspace is chaotic. Maybe you’re still working at the dining table with kids running around.

For Nurturers, this is especially common—they’ll prioritize everyone else’s comfort over their own. So maybe now is the time to carve out your space.

And no, you don’t need a full-blown renovation. I’ve seen people convert closets into podcast studios! Strip of wallpaper, ring light, a mic from Marketplace—it doesn’t have to be expensive. But it’s symbolic: “I take my work seriously. I deserve a space.”

And yes, you can find things second-hand. You can ask for contributions for your birthday. It doesn’t have to cost much—but it sends a message to yourself and to the universe.

Maybe your upgrade is working one day a week in a café, or hiring a babysitter or dog walker for a few hours so you can focus.

Sometimes the first-class upgrade isn’t “stuff”—it’s space. Time. Quiet. Privacy. Energy. All of these matter.

I remember when I was just starting my business, I didn’t quit my job immediately. I deliberately changed jobs—from a high-stress consulting firm to a low-key nonprofit. The pay was lower, but the stress was also lower. Everyone left at 5pm. It was close to home. It was a nine-month maternity leave cover role, and it gave me the space to build my business.

Then, my next upgrade was moving to a 3-day-a-week job at another nonprofit.

That was such a smart, incremental approach. I wasn’t jumping off a cliff—I was creating space for what I wanted.

You might be able to negotiate something similar:

• Four days instead of five
• Remote work
• Reduced hours for the same pay (because you’re more efficient)

On the flip side—and not many people talk about this—sometimes the upgrade is taking on a job.

I’ve had friends recently do this. After COVID, a lot of us were fried. They said, “I’m going to take on a part-time job to stabilise my nervous system while I build my business on the side.” That is 100% valid.

If you don’t yet have the money mindset tools or support system to navigate the ups and downs of entrepreneurship, that might be the upgrade your nervous system needs.

On the flip side, if you already have a business, your upgrade might be discontinuing a product or service that causes you stress.

I did this recently. At the end of last year, in December, I made a big decision that disappointed some people—but it was such a great move for me.

I was in the shower (as you do), and Mark came in and said, “Are you okay if we discontinue the money tracking app next year?” And I said, “Oh my God, YES. Absolutely.”

I had created this free app over a decade ago. But app operating systems constantly change, and we hadn’t updated it in ages. It wasn’t making us money, but it was costing us in support tickets, stress, and assistant time.

I realised: why are we doing this? We don’t want to rebuild it. It’s outdated. And it felt so freeing to let it go, even though I knew some people would be disappointed.

Maybe you have something like that in your business—an offer, a client, a delivery method—that’s draining you.

My friend Leonie Dawson is a great example. She does an annual workbook and over the years she’s delivered it in so many ways:

• Print-on-demand via Amazon
• Printed herself
• Printed in China
• Digital-only
• Printed in the U.S.

Every year she assesses: what works this year? What makes sense for us right now? And she changes it—even if it disappoints some people.

That’s a powerful reminder: it’s your business, your rules.

You don’t have to do it like everyone else. You don’t have to do it like you did last year. And you’re allowed to evolve incrementally.

The same applies if you're thinking, “I really want a new website or brand this year,” but the project feels so massive and overwhelming that you’re stuck in analysis paralysis.

Try this: just upgrade one page this month. You don’t have to do it all at once.

You can be strategic—look at your most visited page and start there. But if that sends you into paralysis again, go with your energy. Ask: “What page do I feel like doing?”

Sometimes the low-hanging fruit is what gives you momentum for the rest.

For the record, the most visited page on my website is my About page. When we were setting goals this year, we looked at data—like what opt-ins were the most popular—and discovered something surprising.

My top opt-in? The book bonuses for Get Rich, Lucky Bitch. I wouldn’t have guessed that! But it’s smart to start there because it’s our biggest source of new leads—and a common path into Money Bootcamp.

That’s an income-producing upgrade. Not just vanity branding.

It’s okay to break your big goals into tiny bite-sized steps. Whether your goal is to make $100K or launch a course, ask:

• What’s the smallest move I can make this month?
• What can I tweak to bring in an extra $500?

Don’t get caught in “How do I build a $100K business?” Instead ask, “What seed can I plant today?”

That shift in mindset—from “I have to do it all now” to “What’s the next step?”—makes a massive difference.

I’ve had people say, “I did my first launch and only got one sale. I’m a failure. I’m never doing this again.”

And I say, “No! You planted a seed.”

My first course back in 2009? One person signed up. And I was so proud. Someone paid me to help them!

My next course? Five people.

The one after that? It became Money Bootcamp.

That launch had somewhere between 20 and 30 people (I can’t remember the exact number anymore!). But now, over 10,000 people have been through that course.

And when people hear that big number, they think, “How can I launch something so perfect and successful?” But it started with one.

Each round, I made it a little better:

• The first version was filmed on my iPad.
• The next one, I hired a cheap videographer and shot it in a hotel room.
• The next one, I invested a little more.

It evolved over time. So ask yourself: What seed are you planting this year?

Maybe it’s finally starting that course. Writing your book. Making your first sale. It all counts.

The next part of this is about making space for what you want.

If you’re saying, “I want to make more money this year,” but you haven’t yet taken practical steps, start there.

You don’t have to know your exact income goal to do this.

Start by:

• Opening a business bank account
• Adding PayPal or Stripe to your website
• Creating a Calendly account or another booking system
• Linking that booking system to your payment processor

These are practical money channels.

Don’t know what to sell yet? Try this:

• Set up a free “Pick My Brain” session on your calendar
• Label it something like “Brainstorming Session” or “Creative Coaching”
• When someone says, “Can I pick your brain?” say, “Yes! Here’s the link.”

That is a massive symbolic upgrade.

You might discover a pattern from those sessions:

• Everyone asks you the same question → boom, there’s a course idea.
• You get clarity on your niche, or your ideal client.

Even if you’ve been doing it for free, now it’s a channel for money.

Another symbolic upgrade? Raise your prices. It can be a powerful energetic shift.

I have tons of free resources at denisedt.com/pricing to help with that.

You might also choose to stop certain free arrangements. Maybe you’ve been running a Facebook group, volunteering, or managing community spaces for free.

Maybe it’s time to press pause so you can focus on your business.

I had this conversation with Mark. He was president of the P&C (Parents & Citizens) at our kids’ school and volunteering for a bunch of things. I said, “This is a big year for us. Can you not do that this year?”

He can go back to it later, of course—but stepping back was a symbolic decision. A declaration of focus.

Another upgrade might be to change your terms and conditions. Maybe you need to:

• Add a cancellation policy
• Set clear boundaries around refunds
• Stop offering extended payment plans that stress you out

These things are so much bigger than admin—they are energetic boundaries that say, “I value my time.”

A few years ago, I made a declaration that all my projects would be profitable. That one decision changed a lot.

My friend Dyan introduced me to a game called Defend Your Portfolio. You get together with other entrepreneurs and go through your offers and investments. You have to defend each one.

It’s such a powerful exercise. You’ll quickly spot what’s not making money, what drains your energy, and what doesn’t align anymore.

You can do this with business friends, even if you’re not investing in real estate or stocks—go through your product suite and ask:

• Is this worth the time?
• Does it feel aligned?
• Would I choose this again?

You don’t have to fix everything overnight, but awareness alone is a huge win.

I remember the first time I said to a client, “Hey, our time is up,” or “Coaching between sessions isn’t included—let’s talk about that on your next call.” That felt terrifying.

But those kinds of boundaries are how you graduate to the next level.

It’s like you can hear the Mario Kart ding—level up! 🎮✨

These decisions are symbolic. They shift your identity.

That’s why I’ve created the Money, Goals and Upgrades Workbook to help guide you through this process. You don’t have to figure it all out alone.

The workbook will help you:

• Set clear, specific goals
• Choose upgrades that make sense for you
• Make sustainable, feel-good progress all year long—not just in January

Go to denisedt.com/jan to download it now. Revisit it each month if you like.

And don’t go away—I’ve got one final thought after this next break.

We’re in January, and you might be wondering, “Hey Denise, how do I become one of those people who sends a testimonial for the podcast?”

I asked Mark to send me the link today—it’s speakpipe.com/denisedt. That’s speakpipe.com/denisedt.

It allows you to upload a short voice testimonial—up to 90 seconds. You can make it shorter if you like. Let us know what you do (not too salesy, please), and share how something you bought from me—like a book or course—has helped you. We’d love to hear from you!

And yes, you might record it in January and it might not come out until September—that’s just how batching works. 😄

Now, my final thought for you is this: we are so hard on ourselves in January. We think, “If I haven’t achieved everything by the end of Q1, I’ve failed.”

But a year is a long time. A lot can shift and change.

So give yourself permission to have a great year. Be gentle. Be kind.

Let your affirmation for the year be:

“It’s my time, and I’m ready for the next step.”

This might be your time for growth.

It might be your time for rest.

It might be your time for creativity, love, or health. It doesn’t have to be just about money.

You’re allowed to have non-binary goals—success doesn’t have to come at the expense of joy.

I believe in you. I’m cheering for you.

I’ll be sharing practical, useful, inspiring content for you all year—so stay tuned. And if you have questions or episode ideas, send them in.

The world is in a weird place, but that doesn’t mean we have to put our dreams on hold. You can help others. You can make money. You can create change.

Why not decide that this is your year?

Thanks for listening—and I’ll see you next time on Chill and Prosper.